All cyclists measure achievement differently. For some, it’s getting the KOM on a ­Strava segment. For urban cyclists, it’s being able to hold a trackstand stock-still, like a pointing dog locking onto a grouse. But one test of skill is arguably the greatest: carrying stuff by bike. Unlike your Suffer Score, it’s a talent that’s useful in everyday life—but like all aspects of cycling, there are benchmarks to achieve on the way to mastery. Here’s your guide to moving through the ranks.

The Accidental Portage
This occurs when someone gives you a stuffed moose head or you can’t pass up a sweet deal on some boxed wine, and the only way to get it home is on two wheels. It can also teach you a crucial physics lesson. With malbec hanging from one grip and chardonnay from the other, you soon discover that the slightest twitch of the bar causes the boxes to sway like pendulums. Eventually, your tasty bargains send you riding into a parked car—which is extra embarrassing if you’re wearing the moose head like a helmet. “I’ll never be humiliated like that again!” you resolve, as you set about equipping yourself. As a cyclist, naturally your first instinct is to copy the professionals. And who carries stuff by bike professionally? Bike messengers!

The Voluminous Bag
So you buy the biggest messenger bag you can find. “Great!” you think. “Now I can haul anything!”

Inevitably, though, you discover the limitations of the voluminous bag. Sure, it’s no problem getting all that wine in there, but once you put the bag onto your body, breathing becomes difficult, which is especially troublesome if you live in a place where there are hills. Also, if the temperature is above freezing you’re going to wind up with a gigantic sweat stain on your back, as well as the telltale Slash of Perspiration across your chest from the bag’s strap. It’s the scarlet letter of bike portaging, like those “ribbons of shame” in the movie Gung Ho. This leads to your next great revelation: “Why not let the bike carry everything for me?”

The Rideable Hand Truck
Have you ever seen a cowboy wearing­ a backpack? Of course not! Cowboys use saddlebags. Suddenly those racks you thought were so dorky start to look appealing.­ You ditch the voluminous bag in favor of some ­waterproof panniers. You stock up on bungee cords. You savor the breeze blowing across your unencumbered torso. You carry more organic groceries than you ever thought possible. Nobody wants to steal your bike because it looks like a garden trellis. It seems like you’ve reached the pinnacle of carrying stuff by bike. But soon you have to confront a fundamental truth about human nature: We accumulate lots of crap.

Those bungee cords end up sitting in your panniers. So does your lock. And that rain jacket you now carry at all times “just in case.” Also a beer, and a pair of flip-flops, because why not? Suddenly your panniers are full before you even leave the house. You start craving a bigger bike. You’re about to reach the top step of...

The Ziggurat of Portaging
Whether you’re pedaling an American-­style longtail, a Danish-style frontal loader, or a Dutch-style bakfiets, you’re no longer carrying stuff by bike: You’re now captaining a terrestrial container ship that just happens to have a chain drive. It’s only a bike in the sense that your car is a radio. But as absurd as life at the top of the Ziggurat of Portaging can be, it’s also undeniably convenient and a lot of fun. No longer will you wonder how you’ll get that Ikea bookcase home. Instead, while you’re unloading a week’s worth of groceries and a used motorcycle, you’ll find wine in your cargo bike that you bought weeks ago, and then forgot about.